Hydrochloric Acid → 4-{[3'-(Aminomethyl)-3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}-3-cyano-N-(1,3-thiazol-2-yl)benzenesulfonamide, hydrochloride salt

HRID 1619604Notes

Reaction equation

HRID 1619604 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:32]4[S:33][CH:34]=[CH:35][N:36]=4)(=[O:30])=[O:29])=[CH:24][C:23]=3[C:37]#[N:38])=[C:17]([C:39]3[N:43]([CH3:44])[N:42]=[CH:41][CH:40]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1)(C)(C)C.[ClH:46]>ClCCl.O1CCOCC1>[ClH:46].[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([S:28]([NH:31][C:32]4[S:33][CH:34]=[CH:35][N:36]=4)(=[O:29])=[O:30])=[CH:24][C:23]=3[C:37]#[N:38])=[C:17]([C:39]3[N:43]([CH3:44])[N:42]=[CH:41][CH:40]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86660858HCID 86660858, compound

Product 1

HCID 566013784-{[3'-(Aminomethyl)-3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}-3-cyano-N-(1,3-thiazol-2-yl)benzenesulfonamide, hydrochloride saltYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl-{[4′-{2-cyano-4-[(1,3-thiazol-2-ylamino)sulfonyl]phenoxy}-3′(1-methyl-1H-pyrazol-5-yl)biphenyl-3-yl]methyl}carbamate (Preparation 77, 380 mg, 0.59 mmol) was dissolved in dichloromethane (20 mL), 4M HCl in 1,4-dioxane (4 mL) was added and the reaction was stirred for 18 hours at room temperature. The reaction mixture was concentrated in vacuo, slurried in cold diethyl ether (20 ml) then filtered to afford the title compound (342 mg, 99%) as a yellow solid as the hydrochloride salt.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationthen filtered

Sources & evidence

ORD record
ord-64cdbdde13f84cd5a1bd6c438d8e10c9
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

Loading…